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Crystallizable polycarbonate material based on carbon dioxide and preparation method thereof

A polycarbonate and carbon dioxide technology, which is applied in the field of polymer materials, can solve the problems of thermal stability of polymer products, poor mechanical properties and transparency, difficult polymer processing, and inability to crystallize, and achieves obvious crystallization effect, improved transparency, and polymerization. The effect of high material regularity

Inactive Publication Date: 2011-11-02
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Japan's Nozaki (J.Am.Chem.Soc.1999, 121, 11008-11009) and the United States' Coates research group (Chem.Commun.2000, 2007-2008) respectively use chiral carbon-containing zinc complexes as catalysts, Catalyzed copolymerization of carbon dioxide and epoxycyclohexane to prepare polycyclohexenyl carbonate with isotactic structure of 60% to 80%, but the obtained polymers are all amorphous, which makes polymer injection molding processing more difficult, and polymer Product thermal stability, mechanical properties, poor transparency and other issues
[0004] In 2006, our research group reported the use of a two-component catalytic system composed of a symmetric chiral tetradentate Schiff base cobalt complex and a quaternary ammonium salt for the asymmetric copolymerization of carbon dioxide and cyclohexane oxide, but obtained Carbonate has only 38% isotactic structure and cannot be crystallized (Macromolecules 2006, 39, 5679-5685)

Method used

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  • Crystallizable polycarbonate material based on carbon dioxide and preparation method thereof
  • Crystallizable polycarbonate material based on carbon dioxide and preparation method thereof
  • Crystallizable polycarbonate material based on carbon dioxide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add in the stainless steel autoclave with an effective volume of 200mL and the ambient temperature in the following order: 0.5×10 -3 Mole (R, R)-SalenCoX(R 1 = T-Bu, R 2 =1-adamantyl, R 3 = T-Bu, R 4 = T-Bu, R 5 , R 6 Yes-(CH 2 ) 4 -, X is acetate anion), 0.5×10 -3 Moles of bis-(triphenylphosphonium) ammonium chloride, 0.25 moles of epoxy cyclohexane, 0.25 moles of (R)-2-methyltetrahydrofuran, control the temperature at -10°C, and then pass in carbon dioxide gas and maintain 0.8MPa After reacting at a constant pressure for 24 hours under magnetic stirring, the unreacted carbon dioxide in the autoclave was slowly released, and a large amount of ether was added to precipitate the polycarbonate. It was filtered, washed with ether for several times, and dried in vacuum to constant weight to obtain 20 g of polycyclohexenyl carbonate white solid. The average molecular weight of the polymer determined by gel permeation chromatography was 18000, and the molecular weight distribut...

Embodiment 2

[0036] Using the same equipment in Example 1, under the same conditions, but after the temperature was lowered to -25°C and reacted for 48 hours, 14 grams of polycyclohexenyl carbonate was obtained, with a molecular weight of 12,000 and a molecular weight distribution of 1.15. The content of carbonate units in the product reaches 99%. by 13 C-NMR analysis found that the polymer had an identical structure exceeding 98%. After a small amount of hydrolyzed polycarbonate was analyzed by chiral gas phase column, it was found that the enantioselectivity of 1,2-cyclohexanediol was 96% (SS / RR= 98 / 2); After the obtained polymer was kept at a constant temperature of 180°C for 5 minutes, and analyzed by DSC, it was found that the glass transition temperature of the polymer was 118°C, the maximum crystal melting peak appeared at 218°C, and the enthalpy of fusion was 27.1 J / g; Thermogravimetric analysis shows that its 50% material decomposition temperature is 310℃.

Embodiment 3

[0038] Using the same equipment in Example 1, under the same conditions, only 0.25 mol of (S)-2-methyltetrahydrofuran was increased to 1.0 mol, and after reacting at -10°C for 24 hours, 12 g of polycyclohexane carbonate was obtained. The olefin ester has a molecular weight of 11,000, a molecular weight distribution of 1.15, and the content of carbonate units in the polymer reaches 99%. by 13 C-NMR analysis found that the polymer had an identical structure exceeding 90%. After a small amount of hydrolyzed polycarbonate was analyzed by a chiral gas phase column, it was found that the enantioselectivity of 1,2-cyclohexanediol was 90% (SS / RR= 95 / 5); After keeping the obtained polymer at a constant temperature of 180°C for 15 minutes, DSC analysis showed that the glass transition temperature of the polymer was 118°C, the maximum crystal melting peak appeared at 217°C, and the melting enthalpy was 13.1 J / g; Thermogravimetric analysis shows that its 50% material decomposition temperat...

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Abstract

The invention belongs to the field of high molecular materials and relates to a crystallizable polycarbonate material based on carbon dioxide and a preparation method thereof. The crystallizable polycarbonate material based on carbon dioxide is characterized in that carbon dioxide and cyclohexene oxide are copolymerized into a crystallizable polycarbonate material with a highly identical stricture under the action of a catalyst. The polycarbonate material has the following characteristics that the content of polycarbonate units in a polymer chain is 90-100%, the identical structure of the polymer is between 88.0% and 99.9%, the tested selectivity of an enantiomer of diol is between 88.0% and 99.9% after the polymer is hydrolyzed with a sodium hydroxide aqueous solution, and the crystallizable polycarbonate material can be obtained after the polymer is subjected to simple thermal treatment. The polycarbonate material provided by the invention has the advantages of high crystallization, high clarity and the like.

Description

Technical field [0001] The invention discloses a crystallizable carbon dioxide-based polycarbonate material and a preparation method thereof, and belongs to the field of polymer materials. Background technique [0002] Carbon dioxide is the main gas that causes the greenhouse effect. At the same time, it is the most abundant and cheap carbon resource on the planet. Its reserves are more than the sum of oil, natural gas and coal. The chemical fixation of carbon dioxide is an important research field of green chemistry. Under the action of a catalyst, carbon dioxide can be copolymerized with alkylene oxide to prepare biodegradable polycarbonate materials. The polymer has excellent oxygen and water barrier properties and can be used as food packaging materials, engineering plastics, rubber additives, adhesives and medical materials. [0003] At present, there are many domestic and foreign patent reports on the copolymerization of carbon dioxide and alkylene oxide to prepare polycarb...

Claims

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Application Information

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IPC IPC(8): C08L69/00C08G64/34
Inventor 吕小兵伍广朋任伟民
Owner DALIAN UNIV OF TECH
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